5495-84-1

Basic information

• Product Name: 2-Isopropylthioxanthone
• Synonyms: SPEEDCURE ITX;QUANTACURE ITX;SPEEDCURE 2-ITX;2-Isopropylthioxanthon;Photocure-Itx;2-Isopropylthioxanthen-9-one;9H-Thioxanthen-9-one, 2-(1-methylethyl)-;2-isopropylthioxantone
• CAS NO: 5495-84-1
• Molecular Formula: C₁₆H₁₄OS
• Molecular Weight: 254.35
• EINECS: 226-827-9
• Product Categories: Functional Materials;Photopolymerization Initiators;Aromatics;Sulfur & Selenium Compounds
• Mol File: 5495-84-1.mol
• Article Data: 14

Chemical Properties

• Melting Point: 76 °C
• Boiling Point: 398.9 °C at 760 mmHg
• Flash Point: 210 °C
• Appearance: /
• Density: 1.199 g/cm³
• Vapor Pressure: 1.43E-06mmHg at 25°C
• Refractive Index: 1.638
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Ethyl Acetate (Slightly)
• Water Solubility: 340μg/L at 20℃
• CAS DataBase Reference: 2-Isopropylthioxanthone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Isopropylthioxanthone(5495-84-1)
• EPA Substance Registry System: 2-Isopropylthioxanthone(5495-84-1)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 20/21-58
• WGK Germany: 3
• Hazardous Substances Data: 5495-84-1(Hazardous Substances Data)

Usage

Chemical Properties

2-Isopropylthioxanthone is light yellow solid with general solubility, effective at low concentration. The absorption wavelength is 250~400nm.

Uses

2-Isopropylthioxanthone is a thioxanthone derivative useful as photoinitiators.

Application

2-Isopropylthioxanthone has been used as an analytical standard for the determination of the analyte in packaged food materials using liquid chromatography-tandem mass spectrometry (LC–MS/MS). It may be used as an analytical standard for the determination of the analyte in milk, fruit drinks and packaged beverages by high performance liquid chromatography (HPLC) coupled to MS/MS and micellar electrokinetic chromatography techniques (MEKC).

General Description

2-Isopropylthioxanthone is a compound, which can play the role of a sulfur type photoinitiator in printing industries and UV-cured inks for food packaging materials.

InChI:InChI=1/C16H14OS/c1-10(2)11-7-8-15-13(9-11)16(17)12-5-3-4-6-14(12)18-15/h3-10H,1-2H3

Synthetic route

Isopropylbenzene (98-82-8) + 2,2'-dithiobenzoic acid (119-80-2) → 2-isopropyl-9H-thioxanthen-9-one (5495-84-1)

Conditions	Yield
With sulfuric acid at 20℃; for 0.5h;	99%
With methanesulfonic acid; zinc In chlorobenzene at 115℃;	89.5%

2-isopropyl thioxanthene → 2-isopropyl-9H-thioxanthen-9-one (5495-84-1)

Conditions	Yield
With tert.-butylnitrite; oxygen; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 20℃; for 12h; Irradiation;	98%
With tert.-butylnitrite; oxygen; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane at 20℃; for 12h; Sealed tube; Irradiation;	98%
With potassium hexafluorophosphate; iron(III) nitrate monohydrate; oxygen In acetonitrile at 80℃; for 2h; Reagent/catalyst; Temperature; Concentration;	96%
In 1,2-dichloro-ethane at 20℃; for 2h; UV-irradiation;	75%
With air In 1,2-dichloro-ethane at 20℃; for 2h; UV-irradiation;	75%

2-(4-isopropylphenylthio)benzoic acid (5495-75-0) → 2-isopropyl-9H-thioxanthen-9-one (5495-84-1)

Conditions	Yield
With sulfuric acid In cyclohexane Solvent; Temperature; Reflux;	91%

Isopropylbenzene (98-82-8) + 2-chlorosulfenylbenzoyl chloride (3950-02-5) → 4-isopropylthioxanthone + 2-isopropyl-9H-thioxanthen-9-one (5495-84-1)

Conditions	Yield
iron(III) chloride In 1,2-dichloro-ethane at 20℃; for 0.5h; Product distribution / selectivity; Friedel Crafts Acylation;	A 9.8% B 88.2%
aluminum (III) chloride In 1,2-dichloro-ethane at -10 - 25℃; for 1 - 1.25h; Product distribution / selectivity; Friedel Crafts Acylation;	A 11.2% B 76%

Isopropylbenzene (98-82-8) + 2,2'-dithiobenzoic acid (119-80-2) + Benzotrichlorid (98-07-7) → 4-isopropylthioxanthone + 2-isopropyl-9H-thioxanthen-9-one (5495-84-1) + 3-isopropylthioxanthone

Conditions	Yield
Stage #1: 2,2'-dithiobenzoic acid; Benzotrichlorid With iron(III) chloride In chlorobenzene at 100℃; for 1h; Inert atmosphere; Stage #2: Isopropylbenzene With aluminum (III) chloride In trans-1,2-dichloroethylene at 20℃; for 1h; Inert atmosphere; Overall yield = 32.8 g;

2-chloro-2'-ethoxy-5'-isopropylbenzophenone → 2-isopropyl-9H-thioxanthen-9-one (5495-84-1)

Conditions	Yield
With copper; sodium carbonate; sulfur In 1,2-dichloro-ethane Solvent; Reagent/catalyst; Reflux;	20.8 g

2-chloro-2'-methoxy-5'-isopropylbenzophenone → 2-isopropyl-9H-thioxanthen-9-one (5495-84-1)

Conditions	Yield
With copper; sulfur; sodium hydroxide In 1,2-dichloro-ethane Solvent; Reagent/catalyst; Reflux;	20 g

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → 2-isopropyl-9H-thioxanthen-9-one 10,10-dioxide (210295-96-8)

Conditions	Yield
With Oxone In methanol; water Heating / reflux;	82%

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → 2-isopropylthioxanthone sulphoxide (482662-60-2)

Conditions	Yield
With cerium(IV)diammonium nitrate In water; acetonitrile at 20℃; for 2.5h;	52.3%
With ammonium cerium(IV) nitrate In water; acetonitrile at 20℃; for 2.5h;	52.3%
With dihydrogen peroxide; trifluoroacetic acid In water at 0 - 23℃; for 12.25h;

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C29H26OS

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate; methanol 2.1: perchloric acid / toluene; water 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -84 °C / Sealed tube; Inert atmosphere 3.2: 1 h / 20 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C30H28OS

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium tetrahydroborate; methanol 2: perchloric acid / toluene; water 3: 0.5 h / 20 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C24H24OS

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate; methanol 2.1: thionyl chloride / Inert atmosphere; Cooling with ice 2.2: Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -84 °C / Inert atmosphere 3.2: 1 h / 120 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C25H26OS

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium tetrahydroborate; methanol 2.1: thionyl chloride / Inert atmosphere; Cooling with ice 2.2: Inert atmosphere 3.1: 2 h / 20 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C16H16OS

Conditions	Yield
With methanol; sodium tetrahydroborate

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → 9-(phenylthio)-2-isopropyl-9H-thioxanthene

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate; methanol 2: perchloric acid / toluene; water View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → 9-(methylthio)-2-isopropyl-9H-thioxanthene

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium tetrahydroborate; methanol 2.1: thionyl chloride / Inert atmosphere; Cooling with ice 2.2: Inert atmosphere View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C27H27O6S(1+)*CF3O3S(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid; dihydrogen peroxide / water / 12.25 h / 0 - 23 °C 2.1: chloroform / 0.5 h / 23 °C 2.2: 2.25 h / 5 - 23 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C26H24O6S

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trifluoroacetic acid; dihydrogen peroxide / water / 12.25 h / 0 - 23 °C 2.1: chloroform / 0.5 h / 23 °C 2.2: 2.25 h / 5 - 23 °C 3.1: sodium hydroxide; water / chloroform / 1.5 h / 23 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C25H22O6S

Conditions	Yield
Multi-step reaction with 3 steps 1.1: trifluoroacetic acid; dihydrogen peroxide / water / 12.25 h / 0 - 23 °C 2.1: chloroform / 0.5 h / 23 °C 2.2: 2.25 h / 5 - 23 °C 3.1: sodium hydroxide; water / chloroform / 1.5 h / 23 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C26H25O6S(1+)*CF3O3S(1-)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid; dihydrogen peroxide / water / 12.25 h / 0 - 23 °C 2.1: chloroform / 0.5 h / 23 °C 2.2: 2.25 h / 5 - 23 °C View Scheme

2-isopropyl-9H-thioxanthen-9-one (5495-84-1) → C25H22O4S

Conditions	Yield
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid; dihydrogen peroxide / water / 12.25 h / 0 - 23 °C 2.1: trifluorormethanesulfonic acid / chloroform / 0.5 h / 23 °C 2.2: 6.25 h / 5 - 23 °C View Scheme

Upstream product

• 5495-81-8 2-(4-ethylpiperazin-1-yl)-N-phenylacetamide 
• 54957-94-7 TERT-BUTYL-N,N-DICHLOROCARBAMATE 
• 54957-90-3 QUINOLINE SULPHATE 
• 54957-86-7 2,3-DICHLORO-6-PICOLINE 
• 54957-84-5 2-CHLORO-6-METHYLNICOTINAMIDE 
• 54957-81-2 3-cyano-2-ethoxy-6-methylpyridine 
• 54957-80-1 3-CYANO-2-FLUORO-6-PICOLINE 
• 54957-66-3 3-(4-ISOPROPYL-PHENYL)-3-OXO-PROPIONIC ACID ETHYL ESTER 
• 54957-63-0 3-[4-(propan-2-yl)benzoyl]-6-[4-(propan-2-yl)phenyl]-2H-pyran-2,4(3H)-dione 
• 5495-75-0 2-CARBOXY-4'-ISOPROPYLDIPHENYL SULFIDE 
• 54957-39-0 6,6,9-trimethyl-1-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-3-ol 
• 54957-21-0 1,1-dimethyl-3-oxo-5-phenyl-2,3-dihydro-1H-pyrazol-1-ium 
• 54957-02-7 3-((2-Mercapto-1-methylpropyl)thio)-2-butanol 
• 549-56-4 QUININE SULFATE 

Downstream Products

• 54958-41-7 2-Isopropyltioxanthone 
• 5495-86-3 4-bromo-N-[4-oxo-3-prop-2-en-1-yl-5-(quinolin-2-ylmethylidene)-1,3-thiazolidin-2-ylidene]benzenesulfonamide 
• 54958-67-7 Levorenone 
• 54958-72-4 Deposiston 
• 5495-87-4 2-(tert-butyl)-9H-thioxanthen-9-one 
• 54959-22-7 (4-nitrothiophenolato)iron(III)-protoporphyrin IX dimethyl ester complex 
• 54959-35-2 potassium [[N,N'-ethylenebis[N-(carboxymethyl)glycinato]](4-)-N,N',O,O',ON,ON']ferrate(1-) 
• 54959-69-2 5-di-(2'-tetrahydropyranosyl)secalonic acid D 
• 549-59-7 tris[(8alpha,9R)-6'-methoxycinchonan-9-ol] bis(arsenate) 
• 54959-85-2 5-(4-CHLOROPHENYL)-5-OXOVALERONITRILE 
• 549-60-0 QUININE PHOSPHATE 
• 5496-04-8 3-Methyl-1-phenyl-4-(piperidinomethylene)-2-pyrazolin-5-one 
• 54960-65-5 N-TRIS[HYDROXYMETHYL]METHYL-4-AMINOBUTANESULFONIC ACID 
• 54960-76-8 2-chloro-5-methylphenanthridin-6(5H)-one 

Recommend Products

• 98-82-8  Isopropylbenzene 
• 119-80-2  2,2'-dithiobenzoic acid 
• 83846-86-0  4-isopropylthioxanthone 
• 3950-02-5  2-chlorosulfenylbenzoyl chloride 
• 482662-60-2  2-isopropylthioxanthone sulphoxide 
• 210295-96-8  2-isopropyl-9H-thioxanthen-9-one 10,10-dioxide 
• 162881-26-7  phenyl bis(2,4,6-trimethylbenzoyl)phosphine oxide 
• 474510-57-1  2-hydroxy-1-(4-(4-(2-hydroxy-2-methylpropionyl)-benzyl)-phenyl)-2-methylpropan-1-one 
• 98-07-7  Benzotrichlorid 
• 5495-75-0  2-(4-isopropylphenylthio)benzoic acid